Thienobenzodiazepinones, pharmaceutical compositions thereof and method of use thereof

Abstract

This invention relates to novel compounds of the formula <IMAGE> (I) wherein R1 is hydrogen or alkyl having from 1 to 4 carbon atoms; R2 is halogen, hydrogen, or alkyl having from 1 to 4 carbon atoms; and R is (1-methyl-4-piperidinyl)methyl, (1-methyl-1,2,5,6-tetrahydro-4-pyridinyl)methyl, 1-methyl-1,2,5,6-tetrahydro-4-pyridinyl, (1-methyl-4-piperidinylidene)-methyl, or (8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-methyl, each of which can optionally have an additional methyl substituent on the heterocyclic ring, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as anti-ulcerogenics.

We claim: 
     
       1. A compound of the formula ##STR10## wherein R 1  is hydrogen or alkyl having from 1 to 4 carbon atoms; R 2  is hydrogen, halogen, or alkyl having from 1 to 4 carbon atoms; and   R is (1-methyl-4-piperidinyl)methyl, (1-methyl-1,2,5,6-tetrahydro-4-pyridinyl)methyl, 1-methyl-1,2,5,6-tetrahydro-4-pyridinyl, (1-methyl-4-piperidinylidene)-methyl, or (8-methyl-8-azabicyclo 3.2.1!oct-3-yl)-methyl, each of which can optionally have an additional methyl substituent on the heterocyclic ring, a diastereoisomer or enantiomer thereof, or a non-toxic, pharmacologically acceptable acid addition salt thereof with an inorganic or organic acid.     
     
     
       2. A compound of claim 1, wherein R 1  and R 2 , which may be the same or different from each other, are each hydrogen or methyl, and   R is (1-methyl-4-piperidinyl)-methyl, 1-methyl-1,2,5,6-tetrahydro-4-pyridinyl, or (8-methyl-8-azabicyclo 3.2.1!oct-3-yl)methyl, a diastereoisomer or enantiomer thereof, or a non-toxic, pharmacologically acceptable acid addition salt thereof with an inorganic or organic acid.     
     
     
       3. 4,9-Dihydro-4- (1-methyl-4-piperidinyl)-acetyl!-10H-thieno 3,4-b! 1,5!benzodiazepin-10-one or a non-toxic, pharmacologically acceptable acid addition salt thereof with an inorganic or organic acid. 
     
     
       4. An anti-ulcerogenic pharmaceutical composition consisting essentially of an inert pharmaceutical carrier and an effective anti-ulcerogenic amount of a compound of claim 1. 
     
     
       5. The method of inhibiting the formation of gastric ulcers in a warm-blooded animal in need thereof, which comprises perorally, parenterally, or rectally administering to said animal an effective anti-ulcerogenic amount of a compound of claim 1.